This one is a good candidate. (“We lost Davy in the Korean War / Still don’t know what for / Don’t matter anymore.”) I know only Joan Baez’s version of it. Another sad one from that Baez album is “Jesse,” written by Janis Ian. (Yeah, “At Seventeen” is a sad one too.)
I would also mention Rickie Lee Jones’ “Last Chance Texaco” and “Comin’ Back to Me” (which I think was a Jefferson Airplane tune originally).
It’s interesting to me that many of my favorite songs are being mentioned here. Leonard Cohen? I love his old stuff; it always cheers me up. “Dress Rehearsal Rag” comes to mind especially. Tom Waits? Possibly my favorite musician on Earth. The Beatles? I like it all, but especially the dark stuff.
“Sunflowers”,“Queen of the Air”,“Pale Green Stars” and “the Twistinside” by Everclear (for the most part every Everclear song is depressing)
“She’s Gone” by NOFX
dead0man
Hey mikeargo, how about every single song on The Trinity Sessions by the Cowboy Junkies? “Misguided Angel”, “Sweet Jane”, “200 Miles”, “I Don’t Get It”, “Blue Moon”. Every single song is the saddest song ever written. My favorite album of all time, BTW.
Second vote for REM’s "Try not to Breathe’-- about an older person deciding that life’s been long enough and telling someone about his memory/existence. Like Rutger Hauer’s speech at the end of Bladerunner about the amazing things he’s seen (god, this is liek a double nerd reference). “Half a world Away,” I think, from the same album is great/depressing, too.
Also the Cowboy Junkies’ entire oeuvre. Jeez. The entire album Trinity Sessions (I think it is called) just makes me go back to bed.
Damn, Lemur, on preview, I note you feel the same way.
Any version of “Stretched on your Grave” (or whatever the name of the traditional song with that lyric is) makes me feel like I’m about to go nuts.
2 Elton John songs - Daniel and Candle in the Wind.
Peter, Paul and Mary - Leaving on a Jet Plane.
Glen Campbell - Wichita Lineman.
Simon and Garfunkel - The Boxer.
Number 1, no questions please, James Taylor - Fire and Rain.
Lonestar - I’m Already There
Air Supply - Goodbye
REO Speedwagon Can’t Fight This Feeling (I know this one isn’t technically a sad song, but I personally find it rather depressing.)
I think I’m about to post the same song in 2 threads back-to-back (the other is If Life Is A Rock And the Radio Rolls Me) but I once played I Honestly Love You sung by Olivia Newton-John after my first case of puppy love ended. BAD mistake! I couldn’t make it throug it without bursting into tears.
There’s only one song that makes me cry — real tears — every single time I hear it. That song is “The Journey On” by Kate Price. It isn’t so much that it’s sad (although it is), but the intense beauty of the lyrics makes me cry. So I don’t know if it’s the saddest song there is, but it sure is one the best sad songs ever.
I also cried listening to Woody Guthrie’s songs “Hobo’s Lullaby” and “I Ain’t Got No Home in this World Anymore”.
Southern trees bear a strange fruit
Blood on the leaves and blood at the root
Black bodies swingin’ in the southern breeze
Strange fruit hangin’ from the poplar trees